Neue [2.2]Paracyclophan‐1,9‐diene aus 1,9(10)‐Dibrom‐[2.2]paracyclophan‐1,9‐dien

Stöbbe, Michael; Reiser, Oliver; Näder, Reinhard; Meijere, Armin de

doi:10.1002/cber.19871201010

Cited by 34 publications

(12 citation statements)

References 22 publications

(1 reference statement)

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“…In general, the conjugation length and the orientation of the chromophores may play a distinctive role in this respect. Moreover, incorporation of a double bond in the tethering aliphatic chain(s) such as cyclophenes and cyclophandienes may alter the geometry of the molecules which may lead to unusual photophysical properties [28][29][30]. In the previous sections, we have demonstrated the unique synthetic approaches and useful physical properties of alternating benzene-furan oligomers.…”

Section: Synthesis Of Furan-containing [N2]cyclophenesmentioning

confidence: 94%

Heterophenes revisited

Luh

Lin

Chou

2008

Pure and Applied Chemistry

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By employing the furan annulation protocol, a new series of furan-containing teraryl [n.2]cyclophenes (n = 2-6 and 12) are prepared. These cyclophenes exhibit chargetransfer character in the absorption spectra and unusually large Stokes shifts in the emission spectra. They have neither particularly strong electron-donating moieties nor electron-withdrawing groups, but exhibit unusual second-order nonlinear optical (NLO) properties. The π-systems in teraryl system and in the bridging double bond are highly twisted. Interaction between these twisted π-systems may account for the significant enhancement in hyperpolarizability. Thiophene analog behaved similarly. The five-membered heteroaromatic rings may not only serve as electron donors, but also may accommodate the appropriate geometry to enable the interactions between the oligoaryl systems and the double bond leading to unusual photophysical and NLO properties.

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Section: Synthesis Of Furan-containing [N2]cyclophenesmentioning

confidence: 94%

Heterophenes revisited

Luh

Lin

Chou

2008

Pure and Applied Chemistry

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“…ROMP of the cyclophanediene 89 forms PPV‐oligomers 32 4 with a P n around 4 (Scheme ). The monomer 89 was prepared by deMeijere and co‐workers69 and ROMP was performed in cyclohexane, in which neither it nor PPV 32 is particularly soluble. It would perhaps have been better to use dichloromethane (DCM) or a similar solvent.…”

Section: Arylenevinylenesmentioning

confidence: 99%

Alkene Metathesis – A Tool for the Synthesis of Conjugated Polymers

Bunz

Mäker

Porz

2012

Macromol. Rapid Commun.

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Alkene metathesis is a superb methodology. We report the progress using alkene metathesis in the synthesis of polymeric organic semiconductors. Three classes of polymers have been synthesized using acyclic diene metathesis (ADMET) or ring opening metathesis polymerization (ROMP), viz., poly(acetylene)s (PA), poly(arylene‐vinylene)s (PAV), and organometallic polymers. For PAs, ROMP of cyclooctatetraenes is best, whereas for PAV, both ADMET and indirect and direct ROMP are viable. Metathesis performs flawlessly with the correct monomers, as molybdenum and particularly the robust Ru carbenes demonstrate. When performing ROMP, one is often rewarded with structurally uniform polymers that can display very low polydispersities. Overall, metathesis is a powerful tool for the preparation of semiconducting polymers.

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“…A highly efficient route to soluble rigid systems with alternating orthogonal arene units was found by utilizing the mixture of 1,1,9,9-and 1,1,10,10-tetrabromo[2.2]paracyclophane (19), which is readily obtained from 1 in 100 g quantities by photobromination [22], as a synthetic equivalent for [2.2]paracyclophane-1,9-diyne. When the tetrabromides 19 were dehydrobrominated with KoBu t in the presence of excess furan, a mixture of the isomeric Diels-Alder products anti-/syn-20 arising from trapping of intermediately formed [2.2]paracyclophaneynes, was obtained in moderate yield.…”

Section: Extended Orthogonal -Systemsmentioning

confidence: 99%

“…Most of the synthetic approaches towards benzoannelated [2.2]paracyclophanes use the Diels-Alder reaction to build up the annelated rings [18,22,29]. [2.2]Paracyclophane-1-ene (32) and [2.2]paracyclophane -1,9-diene (42) can be considered as the simplest dienophiles for this purpose.…”

mentioning

confidence: 99%

Carbon Rich Cyclophanes with Unusual Properties — an Update

König

1998

Topics in Current Chemistry

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Cyclophane chemistry and the research targets in this area have changed over the past two decades. While the unique electronic and structural properties of cyclophanes are still fascinating, more and more attention is now being paid to the function of the molecules, e.g., to the formation of inclusion complexes of large cyclophanes or the use of chiral cyclophanes as auxiliars in asymmetric synthesis. The rigid structures of short bridge cyclophanes has stimulated the synthesis of compounds with extended p-systems. Both their interesting physical properties, e.g., in intramolecular electron transfer processes, and their often beautiful structures of high symmetry are alluring.While synthetic approaches to cyclophanes, their reactivity and inclusion ability have been reviewed extensively, applications of the cyclophane scaffold and its properties are scattered. Therefore the author will focus on the recent developments in the chemistry of cyclophanes that have been used as building blocks for functional devices, as ligands for metal coordination and chiral auxiliaries or chiral ligands in synthesis. It will show that a class of compounds considered esoteric 20 years ago is now even reaching industrial applications. A review with 60 schemes and 122 references.

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Neue [2.2]Paracyclophan‐1,9‐diene aus 1,9(10)‐Dibrom‐[2.2]paracyclophan‐1,9‐dien

Cited by 34 publications

References 22 publications

Heterophenes revisited

Heterophenes revisited

Alkene Metathesis – A Tool for the Synthesis of Conjugated Polymers

Carbon Rich Cyclophanes with Unusual Properties — an Update

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